1,10-Phenanthroline → HCID 21071235, 화합물

HRID 2113068노트

반응식

HRID 2113068 반응식
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])C1C=CC=CC=1.I[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[C:32]([O-:35])([O-])=[O:33].[K+].[K+].N1[C:51]2[C:42](=[CH:43][CH:44]=[C:45]3[C:50]=2N=CC=C3)[CH:41]=CC=1>CS(C)=O.[Cu]I.O.CCOC(C)=O>[CH2:41]([O:35][C:32]([C:11]1([NH2:10])[CH2:16][CH2:15][CH2:14][N:13]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[C:12]1=[O:17])=[O:33])[C:42]1[CH:51]=[CH:50][CH:45]=[CH:44][CH:43]=1

참가 물질

9

반응물 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 13556445Benzyl (2-oxopiperidin-3-yl)carbamateHCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid

생성물 1

HCID 21071235HCID 21071235, 화합물

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

Part A. To a mixture of (2-oxo-piperidin-3-yl)-carbamic acid benzyl ester (1.35 g, 5.44 mmol) and 1-(4-iodo-phenyl)-cyclopropanecarboxylic acid (1.56 g, 5.42 mmol, 1.0 eq) in DMSO (5 mL) was added K2CO3 (3.00 g, 21.73 mmol, 4.0 eq), CuI (0.52 g, 2.74 mmol, 0.5 eq), and 1,10-phenanthroline (0.50 g, 2.74 mmol, 0.5 eq) sequentially. The mixture was heated at 120° C. overnight under N2. After cooling, EtOAc and H2O was added. The mixture was filtered. The filtrate was washed with 1N NaOH. The aqueous layer was acidified with conc. HCl, and extracted with EtOAc (3×). The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give crude 1-[4-(3-benzyloxycarbonyl-amino-2-oxo-piperidin-1-yl)-phenyl]-cyclopropanecarboxylic acid (0.69 g, slightly contaminated with disubstituted compound). LC/MS (ESI) 409.2 (M+H).

후처리

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered
  3. washThe filtrate was washed with 1N NaOH
  4. extractionextracted with EtOAc (3×)
  5. washThe organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-10870804bcc442fea890041807ea6e5b
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524863B2

반응 노트

불러오는 중…